Novak Djokovic is the most successful player in the history of Grand Slam tennis, having won 24 titles.
The Serbian star won his first Major title at the 2008 Australian Open, fifteen years before his most recent Grand Slam success at Flushing Meadows.
Djokovic rarely loses to lower-ranked players at Grand Slam tournaments, with the majority of his defeats coming against his greatest rivals.

The 37-year-old did, however, suffer a shock exit at the US Open last year, as Djokovic lost to Australia’s Alexei Popyrin in the third round.
He was stunned by another underdog at the French Open, six years earlier, who is now considering retirement.
Marco Cecchinato says he will retire from tennis if his results don’t improve in 2025
Italy’s Marco Cecchinato beat Djokovic at the French Open in 2018 to advance to his first career Major semi-final.
Then ranked 72nd on the ATP Tour, Cecchinato embarked on a remarkable run in Paris, capturing the hearts and imaginations of many.
- 2018 French Open SF – Marco Cecchinato lost to Dominic Thiem, 5-7, 6-7, 1-6
- 2018 French Open QF – Marco Cecchinato beat Novak Djokovic, 6-3, 7-6, 1-6, 7-6
- 2018 French Open 4R – Marco Cecchinato beat David Goffin, 7-5, 4-6, 6-0, 6-3
- 2018 French Open 3R – Marco Cecchinato beat Pablo Carreno Busta, 2-6, 7-6, 6-3, 6-1
- 2018 French Open 2R – Marco Cecchinato beat Marco Trungelliti, 6-1, 7-6, 6-1
- 2018 French Open 1R – Marco Cecchinato beat Marius Copil, 2-6, 6-7, 7-5, 6-2, 10-8
His form has tailed off in recent years, however, and the 32-year-old is now ranked 362nd in the world, competing on the Challenger Tour.
Speaking to La Gazzetta dello Sport, Cecchinato looked ahead to a potential retirement at the end of 2025, having played two tournaments in Rwanda recently.
“If they had told me a while ago that I would play there, I wouldn’t have believed it,” he said.

“At the beginning of the year, I challenged myself to give my all to climb up the rankings and play the Slam qualifiers again.
“If it goes badly, in December I will stop knowing that I have done more than I could have imagined.
“I have fulfilled my two childhood dreams: to enter the top 100 and to be the Italian number one.”
With retirement potentially just months away, Cecchinato looked back upon his greatest-ever result, against Djokovic at Roland Garros.

“The tie-break of the fourth set was crazy in terms of emotions,” he said.
“If I had gone to the fifth, I would have lost. I really gave it my all.
“It was a turning point for Italian tennis: many players recognize that, after that defeat, Nole won three Slams in a row.”
Not hiring a ‘super coach’ was the biggest regret of Marco Cecchinato’s tennis career
Cecchinato reached a career-high ranking of 16th in the world and won three tour-level titles.
| Final | Opponent | Result | Score |
| 2021 Emilia-Romagna Open | Sebastian Korda | Loss | 2-6, 4-6 |
| 2020 Sardegna Open | Laslo Djere | Loss | 6-7, 5-7 |
| 2019 Argentina Open | Diego Schwartzman | Win | 6-1, 6-2 |
| 2018 Croatia Open | Guido Pella | Win | 6-2, 7-6 |
| 2018 Hungarian Open | John Millman | Win | 7-5, 6-4 |
Failing to win more during his 10+ year professional career, the Italian now reveals his biggest regret from his time in tennis.
“I needed to add a super coach to my team in the best period,” said Cecchinato.
“I worked very well with [Simone] Vagnozzi and [Umberto] Ferrara, but Simone was in his first experience.
“I needed a different figure, who could identify certain weaknesses in my character and help me overcome them.”

Cecchinato thinks he needed a coach who would’ve challenged his attitude at times.
“The pressure overwhelmed me and then I’m a bit lazy, sometimes I slowed down in training when I needed to push harder,” he said.
“I followed my nature. The ease of play and the good hand fooled me a bit because I thought that would be enough.
“But instead it wasn’t. I repeat: my fault.”
The world number 362 admits a coaching change in 2019 was too late, as he was ‘no longer there.’

“I entrusted myself to Uros Vico, a very good coach and a splendid person, but I was no longer there,” said Cecchinato.
“I was dazed, too nervous.
“I lost games that I almost won: I still don’t understand how.”
Cecchinato last appeared at a Challenger event in Monza, Italy, losing in qualifying to Bulgaria’s Dimitar Kuzmanov.
It remains to be seen where Cecchinato will appear next, as his fans will no doubt hope that he rediscovers his best form and changes his mind about retirement.
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